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During Herb Powell's visit with the Simpson family, they all played Monopoly. Herb became bankrupt in the game when he landed on Ventnor Avenue, which Lisa owned.[2]

When Marge told her family they didn't need TV to have family fun, she made them play Monopoly. Lisa then asked which version they would play and Marge decided to stick with original Monopoly as the game is crazy enough as it is, because of how an iron can become a landlord (referring to the iron playing piece). They started to play the game but when Lisa tried to build a house on her property, she found that they're all gone. Maggie had them stuffed, chipmunk-like, in her cheeks. When it was Homer's turn he rolled the dice and advanced his piece to Marvin Gardens which Bart had built a mini-compound of hotels and houses on. Homer struggles to pay the rent. Lisa pointed out that the hotels were made of Lego and Bart was cheating. Marge stated it was probably an accident. Lisa thought that Marge defended Bart just because he bought her a house on St. James Place. Bart and Homer start to fight before Lisa and Marge start to fight with them. Maggie called the police. When the police arrived the top hat piece from Monopoly had smashed through the front window. Lou said this was another case of Monopoly-related violence, prompting Chief Wiggum to say he wondered how the Parker Brothers slept at night.[3]